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(+)-boldine
4H-dibenzo(de,g)quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (6aS)-

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CAS Number: 476-70-0Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:207-509-9
FDA UNII: 8I91GE2769
Nikkaji Web:J312.540H
Beilstein Number:0094036
MDL:MFCD00135040
XlogP3-AA:2.70 (est)
Molecular Weight:327.38017000
Formula:C19 H21 N O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Google Patents:Search
US Patents:Search
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Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 162.00 to 165.00 °C. @ 760.00 mm Hg
Boiling Point: 529.35 °C. @ 760.00 mm Hg (est)
Flash Point: 525.00 °F. TCC ( 273.90 °C. ) (est)
logP (o/w): 0.837 (est)
Soluble in:
 water, 56.14 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Boldine 97%
BOC Sciences
For experimental / research use only.
Boldine >98%
Odor: characteristic
Use: Boldine is an natural alkaloid of the aporphine class found in the boldo tree and in Lindera aggregata. Boldine exhibits the activity of antioxidant that effectively protects against free radical induced lipid peroxidation or enzyme inactivation. anti-oxidant; antipyretic; anti-inflammatory
Carbosynth
For experimental / research use only.
(+)-Boldine
Coompo
For experimental / research use only.
Boldine from Plants ≥96%
ExtraSynthese
For experimental / research use only.
Boldine (HPLC) ≥90%
Santa Cruz Biotechnology
For experimental / research use only.
Boldine ≥ 98%
Sigma-Aldrich
For experimental / research use only.
Boldine
analytical standard
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50 145 mg/kg
United States Patent Document. Vol. #4185119

intravenous-mouse LD50 90 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES CARDIAC: CHANGE IN RATE VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Annales Pharmaceutiques Francaises. Vol. 38, Pg. 537, 1980.

oral-mouse LD50 450 mg/kg
VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES CARDIAC: CHANGE IN RATE
Annales Pharmaceutiques Francaises. Vol. 38, Pg. 537, 1980.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for (+)-boldine usage levels up to:
 not for fragrance use.
 
Recommendation for (+)-boldine flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):476-70-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10154
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(6aS)-1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol
Chemidplus:0000476700
RTECS:CE0750000 for cas# 476-70-0
 
References:
 (6aS)-1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):10154
Pubchem (sid):134973663
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C09365
HMDB (The Human Metabolome Database):HMDB39085
FooDB:FDB002096
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 bay laurel leaf
Search Trop Picture
 boldo
Search Trop Picture
 sassafras
Search Trop Picture
 
Synonyms:
 aprophine alkaloid
(S)-boldine
 boldine-chloroform
4H-dibenzo(de,g)quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (6aS)-
4H-dibenzo(de,g)quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (S)-
4H-dibenzo[de,g]quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (6aS)-
4H-dibenzo[de,g]quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (S)-
(9S)-4,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,13,15-hexaene-5,15-diol
(6aS)-1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol
(S)-1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol
 

Articles:

PubMed:[Behavioural impairments and hallucinations after consumption of boldo leaf infusions].
PubMed:A novel UPLC-MS/MS method for sensitive quantitation of boldine in plasma, a potential anti-inflammatory agent: application to a pharmacokinetic study in rats.
PubMed:Surface enhanced Raman scattering study of the antioxidant alkaloid boldine using prismatic silver nanoparticles.
PubMed:Immunomodulatory effect of an isolated fraction from Tinospora crispa on intracellular expression of INF-γ, IL-6 and IL-8.
PubMed:Natural products as potential human ether-a-go-go-related gene channel inhibitors - screening of plant-derived alkaloids.
PubMed:Evaluation of cytotoxic and chemotherapeutic properties of boldine in breast cancer using in vitro and in vivo models.
PubMed:Antiplasmodial and antioxidant isoquinoline alkaloids from Dehaasia longipedicellata.
PubMed:Natural compounds boldine and menthol are antagonists of human 5-HT3 receptors: implications for treating gastrointestinal disorders.
PubMed:Boldine and related aporphines: from antioxidant to antiproliferative properties.
PubMed:Boldine prevents renal alterations in diabetic rats.
PubMed:Boldine induces cell cycle arrest and apoptosis in T24 human bladder cancer cell line via regulation of ERK, AKT, and GSK-3β.
PubMed:Boldine improves endothelial function in diabetic db/db mice through inhibition of angiotensin II-mediated BMP4-oxidative stress cascade.
PubMed:Development of an HPLC fluorescence method for determination of boldine in plasma, bile and urine of rats and identification of its major metabolites by LC-MS/MS.
PubMed:Batch and Continuous Ultrasound Assisted Extraction of Boldo Leaves (Peumus boldus Mol.).
PubMed:Boldine protects endothelial function in hyperglycemia-induced oxidative stress through an antioxidant mechanism.
PubMed:Applied biological and physicochemical activity of isoquinoline alkaloids: oxoisoaporphine and boldine.
PubMed:Acetylcholinesterase inhibition, antioxidant activity and toxicity of Peumus boldus water extracts on HeLa and Caco-2 cell lines.
PubMed:(-)-Kunstleramide, a new antioxidant and cytotoxic dienamide from the bark of Beilschmiedia kunstleri gamble.
PubMed:The aporphine alkaloid boldine improves endothelial function in spontaneously hypertensive rats.
PubMed:Anti-acetylcholinesterase, anti-α-glucosidase, anti-leishmanial and anti-fungal activities of chemical constituents of Beilschmiedia species.
PubMed:Alkaloids from the Chinese vine Gnetum montanum.
PubMed:Boldo prevents UV light and nitric oxide-mediated plasmid DNA damage and reduces the expression of Hsp70 protein in melanoma cancer cells.
PubMed:(+)-Kunstlerone, a new antioxidant neolignan from the Leaves of Beilschmiedia kunstleri gamble.
PubMed:Lancifoliaine, a new bisbenzylisoquinoline from the bark of Litsea lancifolia.
PubMed:In vitro cytotoxic evaluation of a novel phosphinyl derivative of boldine.
PubMed:New alkaloid antibiotics that target the DNA topoisomerase I of Streptococcus pneumoniae.
PubMed:Cytotoxic thiocarbamate derivatives of boldine.
PubMed:Quantitative analysis of boldine alkaloid in natural extracts by cyclic voltammetry at a liquid-liquid interface and validation of the method by comparison with high performance liquid chromatography.
PubMed:Direct identification of phenolic constituents in Boldo Folium (Peumus boldus Mol.) infusions by high-performance liquid chromatography with diode array detection and electrospray ionization tandem mass spectrometry.
PubMed:The aporphine alkaloid boldine induces adiponectin expression and regulation in 3T3-L1 cells.
PubMed:(+)-N-(2-hydroxypropyl)lindcarpine: a new cytotoxic aporphine isolated from Actinodaphne pruinosa Nees.
PubMed:[Simultaneous determination of four alkaloids in Lindera aggregate by high performance liquid chromatography].
PubMed:Alkaloids from Lindera aggregata.
PubMed:Grandine A, a new proaporphine alkaloid from the bark of Phoebe grandis.
PubMed:Effect of boldo (Peumus boldus Molina) infusion on lipoperoxidation induced by cisplatin in mice liver.
PubMed:Boldine: a potential new antiproliferative drug against glioma cell lines.
PubMed:Simultaneous determination of four alkaloids in Lindera aggregata by ultra-high-pressure liquid chromatography-tandem mass spectrometry.
PubMed:5-Hydroxytryptamine2A receptor binding activity of compounds from Litsea sessilis.
PubMed:Antioxidant and pro-oxidant properties of boldine on hippocampal slices exposed to oxygen-glucose deprivation in vitro.
PubMed:Aporphine metho salts as neuronal nicotinic acetylcholine receptor blockers.
PubMed:Characterization of isoquinoline alkaloids from Neolitsea sericea var. aurata by HPLC-SPE-NMR.
PubMed:Studies of Genetic Variation of Essential Oil and Alkaloid Content in Boldo (Peumus boldus).
PubMed:Advances in development of dopaminergic aporphinoids.
PubMed:Are extraction methods in quantitative assays of pharmacopoeia monographs exhaustive? A comparison with pressurized liquid extraction.
PubMed:Antihyperglycemic effect of aporphines and their derivatives in normal and diabetic rats.
PubMed:Sensitive quantification of apomorphine in human plasma using a LC-ESI-MS-MS method.
PubMed:Antinociceptive and free radical scavenging activities of alkaloids isolated from Lindera angustifolia Chen.
PubMed:[Alkaloids from the root of Lindera angustifolia].
PubMed:8-NH2-boldine, an antagonist of alpha1A and alpha1B adrenoceptors without affinity for the alpha1D subtype: structural requirements for aporphines at alpha1-adrenoceptor subtypes.
PubMed:Boldine and its antioxidant or health-promoting properties.
PubMed:Photostability and photoprotection factor of boldine and glaucine.
PubMed:Effect of boldine, secoboldine, and boldine methine on angiotensin II-induced neutrophil recruitment in vivo.
PubMed:Structure-affinity relationships of halogenated predicentrine and glaucine derivatives at D1 and D2 dopaminergic receptors: halogenation and D1 receptor selectivity.
PubMed:Cytotoxic and antitumor potentialities of aporphinoid alkaloids.
PubMed:Photochemistry of phytoalexins containing phenalenone-like chromophores: photophysics and singlet oxygen photosensitizing properties of the plant oxoaporphine alkaloid oxoglaucine.
PubMed:Reactive oxygen species (ROS) generation inhibited by aporphine and phenanthrene alkaloids semi-synthesized from natural boldine.
PubMed:Alkaloids from Cassytha filiformis and related aporphines: antitrypanosomal activity, cytotoxicity, and interaction with DNA and topoisomerases.
PubMed:A novel alkaloid antioxidant, Boldine and synthetic antioxidant, reduced form of RU486, inhibit the oxidation of LDL in-vitro and atherosclerosis in vivo in LDLR(-/-) mice.
PubMed:Inhibitory action of conventional food-grade natural antioxidants and of natural antioxidants of new development on the thermal-induced oxidation of cholesterol.
PubMed:Spectroscopic study of antileishmanial drug incubated in the promastigotes of Leishmania mexicana.
PubMed:Sipaucins A-C, sesquiterpenoids from Siparuna pauciflora.
PubMed:Free-radical scavengers and antioxidants from Peumus boldus Mol. ("Boldo").
PubMed:Effects of some antioxidative aporphine derivatives on striatal dopaminergic transmission and on MPTP-induced striatal dopamine depletion in B6CBA mice.
PubMed:Protection against UVB irradiation by natural filters extracted from lichens.
PubMed:Affinity profile at alpha(1)- and alpha(2)-adrenoceptor subtypes and in vitro cardiovascular actions of (+)-boldine.
PubMed:Structure-activity relationship studies with (+/-)-nantenine derivatives for alpha1-adrenoceptor antagonist activity.
PubMed:Protective effect of boldine on dopamine-induced membrane permeability transition in brain mitochondria and viability loss in PC12 cells.
PubMed:Chemoprotective activity of boldine: modulation of drug-metabolizing enzymes.
PubMed:Release of intermediate reactive hydrogen peroxide by macrophage cells activated by natural products.
PubMed:Free-radical-induced inactivation of lysozyme and carbonyl residue generation in protein are not necessarily associated.
PubMed:Protective effect of boldine on oxidative mitochondrial damage in streptozotocin-induced diabetic rats.
PubMed:Protective effects of boldine against free radical-induced erythrocyte lysis.
PubMed:Biological disposition of boldine: in vitro and in vivo studies.
PubMed:Halogenated boldine derivatives with enhanced monoamine receptor selectivity.
PubMed:Toxicological evaluation of the hydro-alcohol extract of the dry leaves of Peumus boldus and boldine in rats.
PubMed:Boldine action against the stannous chloride effect.
PubMed:Dry plant extracts loaded on fumed silica for direct compression: preparation and preformulation.
PubMed:Halogenated derivatives of boldine with high selectivity for alpha1A-adrenoceptors in rat cerebral cortex.
PubMed:Biochemical and behavioral effects of boldine and glaucine on dopamine systems.
PubMed:Glaucine analogues as inhibitors of mouse splenocyte activity.
PubMed:Antipoliovirus structure-activity relationships of some aporphine alkaloids.
PubMed:Studies on neuromuscular blockade by boldine in the mouse phrenic nerve-diaphragm.
PubMed:Effects of boldine on mouse diaphragm and sarcoplasmic reticulum vesicles isolated from skeletal muscle.
PubMed:Inhibition of eukaryote protein kinases by isoquinoline and oxazine alkaloids.
PubMed:Protective effect of boldine in experimental colitis.
PubMed:Antiplatelet effects of some aporphine and phenanthrene alkaloids in rabbits and man.
PubMed:A possible structural determinant of selectivity of boldine and derivatives for the alpha 1A-adrenoceptor subtype.
PubMed:The effect of S-(+)-boldine on the alpha 1-adrenoceptor of the guinea-pig aorta.
PubMed:Determination of lauraceous aporphine alkaloids by high-performance liquid chromatography.
PubMed:Novel liquid chromatographic assay for the low-level determination of apomorphine in plasma.
PubMed:Cytoprotective and antioxidant effects of boldine on tert-butyl hydroperoxide-induced damage to isolated hepatocytes.
PubMed:Antiplatelet and vasorelaxing actions of some aporphinoids.
PubMed:The inhibitory effects of boldine, glaucine, and probucol on TPA-induced down regulation of gap junction function. Relationships to intracellular peroxides, protein kinase C translocation, and connexin 43 phosphorylation.
PubMed:Boldine prevents human liver microsomal lipid peroxidation and inactivation of cytochrome P4502E1.
PubMed:Structure-antioxidative activity relationships in benzylisoquinoline alkaloids.
PubMed:Anti-inflammatory and antipyretic effects of boldine.
PubMed:Mechanisms of vasorelaxation induced by N-allylsecoboldine in rat thoracic aorta.
PubMed:Effects of boldine on cellular immune functions in vitro.
PubMed:Evaluation of the genotoxic potential of the alkaloid boldine in mammalian cell systems in vitro and in vivo.
PubMed:Trypanocidal effect of boldine and related alkaloids upon several strains of Trypanosoma cruzi.
PubMed:Determination of boldine in drug formulations by first-derivative synchronous spectrofluorimetry.
PubMed:Boldo and boldine: an emerging case of natural drug development.
PubMed:Iron-reducing and free-radical-scavenging properties of apomorphine and some related benzylisoquinolines.
PubMed:Different mechanism of relaxation induced by aporphine alkaloids in rat uterus.
PubMed:Determination of boldine in plasma by high-performance liquid chromatography.
PubMed:Selective action of two aporphines at alpha 1-adrenoceptors and potential-operated Ca2+ channels.
PubMed:Antioxidant action of benzylisoquinoline alkaloids.
PubMed:Inhibition of rat liver microsomal lipid peroxidation by boldine.
PubMed:Inhibition of nonenzymic lipid peroxidation by benzylisoquinoline alkaloids.
PubMed:Activity of boldine on rat ileum.
PubMed:Genotoxicity of the boldine aporphine alkaloid in prokaryotic and eukaryotic organisms.
PubMed:Antioxidant properties of the alkaloid boldine in systems undergoing lipid peroxidation and enzyme inactivation.
PubMed:Hepatoprotective and anti-inflammatory effects of a traditional medicinal plant of Chile, Peumus boldus.
PubMed:Genotoxic effect of alkaloids.
PubMed:A study of the adrenergic activity of the alkaloids boldine and glaucine.
PubMed:Neuroleptic-like, anticonvulsant and antinociceptive effects of aporphine alkaloids: bulbocapnine, corytuberine, boldine and glaucine.
PubMed:Alkaloids of Litsea wightiana1.
PubMed:Voltammetric study of boldine on stationary platinum electrode.
PubMed:Toxic alkaloids and their interaction with microsomal cytochrome P-450 in vitro.
PubMed:[Determination of boldine by HPLC (high pressure liquid chromatography) in Boldus extracts].
PubMed:Biosynthesis of boldine (1,10-dimethoxy-6aalpha-aporphine-2,9-diol).
PubMed:Fluorimetric analysis of alkaloids. Determination of serpentine, yohimbine, and boldine.
PubMed:Stereochemical preferences for curarimimetic neuromuscular junction blockade I: enantiomeric monoquaternary amines as probes.
PubMed:[Densitometric determination of boldine in boldo extracts].
PubMed:[Determination of boldine in Folium boldo and in the commercial preparation Boldiné Houdé].
PubMed:[A colored reaction of boldine].
PubMed:[Colorimetric determination of boldine].
 
Notes:
Alkaloid from Sassafras and the leaves of Peumus boldus (boldo). Flavouring ingredient
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